


Our Special Agreement...Plus Two

by Lolgegecat



Category: Supernatural
Genre: ((and real thing)), BLOWJOBS (the shot), Castiel is your lover...of sorts, Collar Wearing (chp 2), Dean is Mechanic, EVERYONE LOVES FACEBOOK!, F/M, May turn into a series...DEPENDS!, Oral (female and male receiving), Reader is a Millionaire!, Reader is in a "special agreement" with Castiel, sam is lawyer
Language: English
Status: In-Progress
Published: 2017-01-27
Updated: 2018-02-21
Packaged: 2018-09-20 04:54:27
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 12,411
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9476591
Author URL: https://archiveofourown.org/users/Lolgegecat/pseuds/Lolgegecat
Summary: Y/N and Castiel meet while Castiel travels. While they may have met in Vegas, their actions certainly don't stay there...Castiel has not seen or talked to the boys in a long time, so, asking his partner-of-sorts (You), if he can invite them over, with a special idea in mind. things start off rocky once they arrive. But before the weekend is over, all four of you will be rocking! ;)





	1. Reunions...and First Meetings

**Author's Note:**

> I have no idea where this came from. I am proud of it, though a little disgusted at my pride. If anyone would like to see specific kinks, feel free to comment some! I am open.

**Message from Castiel Novak** in **Winchester/Novak Group Chat**

 

 **Castiel N –** Boys! I apologize for my long and unexplained absence. Your Facebook pages indicated that you are not doing well in your romantic endeavors. I would like to invite you to my remote home in Colorado for the weekend. Catch up and other activities. If I receive a notification of your interest, I will text you the address. Please only come together. I will turn one away if the other is not there. Hope to hear back soon!

 

 

As Sam and Dean looked toward the sizable manor, not quite a mansion and not quite a house, they knew that Castiel had invited them to something big. The message had seemed pretty sketchy, but in all the years they've known Cas, his wording can be quite...strange. They were both so excited to see their friend, that they almost forgot about his mentions of their Facebook pages. It seemed like Cas was always watching, looking over them no matter what happened.

 

The trusty Impala drove up the long driveway, coming to rest the door of a two car garage, the farthest one from the house. The boys looked at each other. Dean was the first to speak.

 

“What do you think he's getting us into?” Dean looked to be smiling, but had a small hint of apprehension in his eyes.

 

“Nothing major, probably.” Sam replied, looking to the house with aw and getting out.

 

“Well that helps a lot.” Dean muttered, before following the younger Winchester's lead. They grabbed their respective bags from the trunk, and walked the winding walkway towards the door. They both argued with the other through eye-contact, before Sam sighed and pushed the doorbell. What sounded to be trumpets that you would hear at a royal court announcing the king were heard, and Dean stifled a laugh, while Sam gave a half bitch-face.

 

The didn't wait for two long when the door opened, revealing Castiel, clad in a fuzzy crimson robe, while underneath was a white tee-shirt, and boxers. He smiled at the two, nearly knocking them over the glomp them with a big hug, one Winchester for each arm.

 

“Boys,” He said when he finally pulled back, The grin not lost on his features. He stepped back inside and motioned for them to come in. “Welcome, to mi casa.”

 

The boys felt like they were walking into a dream. On the far wall held a staircase, the wall protecting it looking like marble. To the right there was a parlor, with a huge computer setup Markiplier would be proud of, a grand piano and a huge couch. To the left there was another elevated part, where couches and a coffee table sat, along with a bookshelf the reached almost halfway to the tall ceiling. They could also see the hint of a dining room from the first few steps in.

 

“Boys, no need to be shy. As they say, 'mi casa is su casa'.” Castiel walked toward one of the couches on the elevated ground, beckoning the boys to do the same. “Leave those bags there, you can take them up to your rooms later.

 

The brothers had a sense of surprise and shock. Dropping their bags, they walked over to the couch across from Cas, almost in a trance as the took everything in.

 

“Would you boys like anything to drink?” Cas questioned, tilting his head.

 

Sam was about decline before Dean spoke. “A bottle of your finest beer!” He laughed. Sam looked at him before shaking his head. “Come on Sammy! Live!” Dean picked up on his brother's behavior, punching him on the shoulder. Sam winced before smiling.

 

“Make that two, please.” Sam grinned, earning an 'atta boy!' from Dean.

 

Cas smiled at their antics. “Good, cause that's all we serve here!” He laughed as well. He made no move to get up, which only confused the brothers further, before they heard small clinks coming from an area further than the dining room.

 

The boys failed hiding their utter surprise when you skipped into the room. Light pink silk robe tied but only ending an inch or two from your hips. It was slightly sheer, so they also got an idea of the white lingerie you wore underneath it. Handing a beer toward Cas, he great-fully grabbed it, hand brushing over your knuckles as he did. You giggled, before turning toward the boys, and bending over the coffee table, the opened beers in your hands just in their reach. In your waist-bend, they got an eyeful of your cleavage, while Cas got the wonderful sight of your ass. The boys reached for their drinks, Sam uttering out a breathy “Thanks.” You smiled before stretching back up, your height quite short from all of them, but you basically radiated in front of the boys, demanding their attention. You shot them a wink before walking back toward the kitchen.

 

As they all watched your departure, Sam noticed how dry his throat was, and took a swig of his beer. Dean was nearly halfway done with his bottle before he came up for air. Cas still watched their reactions, sipping appreciatively on his drink before Dean broke the silence.

 

“ _That's_ your _Wife!?”_ He sounded so flabbergasted. Sam elbowed him in the stomach, eyes trying to tell him that that was rude. Dean shrugged before moving his hands in a gesture that made it look like he was calling attention to a work of art. And in his mind, he was. Cas just chuckled before answering the question.

 

“Nope.” The brothers looked shocked, though Dean still looked slightly hopeful.

 

“Girlfriend?” Sam asked, just as you came back into the room, a bubbly looking drink in your hand, straw in your mouth.  


“Not at all.” Cas replied. They both would have accepted that answer, had you not come into the sitting area and plopped yourself right onto Castiel's lap. Cas's arm came around you, your head nuzzling into his neck, straw still in your mouth.

 

“Uh...” Sam looked slightly uncomfortable, not sure what this was. Dean was also uncomfortable, but more in the sense of the growing erection between his legs.

 

“Sweetheart.” Cas spoke, and your head moved up to meet his eyes. He had a stern look, but also a playful one, so you knew you weren't in _that_ much trouble. “That's rude of you! You haven't introduced yourself to our guests!” With a slight encouraging smack on your rear, you stood up, waist bending once again to reach the two.

 

“My apologies.” You sounded so formal it was once again another surprise. “Though I haven't been in the room long enough to get to do that,” You shot a playful glare at Cas, before turning back to the boys. “My name is Y/N Y/L/N. Just Y/N will work.” You smiled, extending your hand out. “And you are?”

 

Sam barely had time to fight Dean's hand away as he reached for yours. Your hands were small and frail compared to his. “Sam,” His voice sounded a little wrecked, and he cleared his throat. “Sam Winchester.” You smiled and looked into his eyes, mesmerizing him with the sparkling E/C hue. He was shocked back to reality with your firm handshake. He inwardly cursed himself, remembering first impressions are everything.

 

Dean clearly had no idea what that meant. When it was his turn, he gently grabbed your hand, leaning forward to place a kiss on your knuckles. You giggled and blushed. When he looked into your eyes, he gave a quick wink. “Dean, Winchester.”

 

Okay, maybe he had a good idea.

 

Pulling back, you gave a slight curtsy, lifting up the already short robe to reveal your lacy white panties and the smooth skin of your stomach. While Sam and Dean looked like they wanted both to run for the hills and take you to bed, Cas's eyes were full of pride and controlled lust. He sat his half-full beer bottle on the coffee table and pulled you back to sit on his lap, one hand wrapping around your waist while the other played with the knot on the robe. You relaxed against him, your hands weaving themselves behind his head and into his hair, your head resting against his shoulder.

 

“I'm sure you have a lot of questions.” Cas smirks, noticing his guest's eyes are not on him, but on you. Your legs parted past his as he sat, his hand holding you toward him massaging any skin he could find. “So BOYS.” the harsh staccato of his voice brought their attention back to him. “Ask away.” He gave another smile, this one seeming a little more dark than the last.

 

Sam cleared his throat. Looking to his and his brother's position, both leaning forward with their elbows on their knees, hands supporting their heads. Sam cursed under his breath, leaning back against the couch and putting his hand on his lap. Realizing then how bad it was that his legs were spread, his hardening cock forcing his jeans to become tighter, he crossed an ankle over his knee. It was uncomfortable, but at least it was common decency.

 

Dean hadn't moved an inch. Though he was the first to speak.

 

“How did you two meet?” It seemed innocent enough, but your sharp intake of breath and Castiel grinning like a Cheshire cat, told them it was anything but.

 

“Oh, that,” He gave a guttural hum of approval at the memory, his cock stirring as he remembered that day, or rather, that _night._ “That was one hell of a day! You see, it started out in Vegas...

 

~~FLASHBACK~~

 

Castiel had been wandering around the casino for quite sometime. His normal trench-coat the he wore decorated a chair in his hotel room. His blue tie traded in for a slim black one. He looked good enough to eat. Though he himself was looking for someone to fill his hunger...

 

They're seemed to be some commotion in the concert hall, open to everyone that night. He decided to go check it out, hearing music as he neared ever closer to the open doors. Peeking inside, he noticed there was a jazz band playing, their tunes winding their way around the dance hall. Without thinking, he walked in, taking in the sea of people that sat around tables and danced in the middle towards the stage. He walked to the bar on the other corner of the room, sitting in a stool and ordering himself a hard cider. He turned around to gaze once more, watching as older couples swayed to the beat, and younger couples talking, looking annoyed, or making out against the wall. He smiled, for he used to be one of them. His drink having arrived, he turned to retrieve it, about to turn back when an arm pushed against his chest. His drink had not spilled, for which he was thankful. He looked to the owner of said arm to notice it covered in a white glove.

 

The girl, or _woman_ , as he could now see, looked annoyed, tired, and ready to cry. He held in his berating words, instead offering some kind ones.

 

“Are you alright, Miss?” He asked. He could only see your side, but he noticed that your dress was backless and had quite a slit in the skirt, a good three-fourths of your leg showing. You looked toward him, acknowledging his presence, before turning back to the bar, ordering yourself a whiskey sour. Sitting in the chair next to him, he stared at you, watching your movements. He continued to watch as you gulped most of your drink down, giving a sigh, before looking back at him.

 

“Hello, Sir.” You said, putting on a bravado he could see right through. “My apologies for wrinkling your shirt,” Cas looked down to notice little wrinkles running through his shirt, but payed them no mind as he looked back to you.

 

“No apology needed, Miss.” He said, holding out the last word, wanting you to give him your name.

 

“Y/N, Sir. Y/N L/N.” You gently put one of your white gloved hands out, the other holding your drink. Castiel took your hand gently in his, leaning down to kiss the bright sapphire ring that wrapped around your index finger.

 

“Castiel Novak.” He spoke as he moved back up. Looking at your jewel encrusted thick halter top part of your dress, scanning up your face, your lips, your cheeks, nose, and finally your eyes. You still looked upset, but he thought he might be fixing that.

 

“Pleasure.” You smiled tightly. Eyes still sparkling with the possibility of tear shed.

 

“I'd say, 'the pleasure is all mine,' but you looked more pained when you said that.” Castiel voiced. Your shoulders fell back, forgetting about your facade.

 

“I'm sure I did.” You laughed slightly, dabbing your eyes with a nearby cloth napkin.

 

“If you don't mind me asking, what brought you to such a state of distress?” Castiel was interested. Your last name echoed in his mind, as he tried to remember where he had heard it before...

 

You gave a bitter laugh, before looking out at the crowd. You ducked and pulled Castiel's sleeve, making him duck with you, he was surprised, but at least he was making progress. You pointed to a man. He had thick eyebrows and gray hair, and small gray goatee framing his mouth.

 

“My father.” You sighed, before noticing your hand wrapped around Castiel's sleeave, letting it go instantly.

 

“He isn't hurting you, is he?” He asked, certainly hoping that wasn't the case.

 

“No, he is just,” You looked for the words. “'Attempting to help me win at life.'” You said around air-quotes. Castiel chuckled, and you found that you enjoyed the sound.

 

“How so?”

 

“Trying to find me a suitor.” You grumbled, downing the rest of your sour. “He thinks he has the right to dictate my life and send me off with these men. They either want a good fuck, excuse my french, or a baby-maker!” You groaned at the idea. Sure babies were cute and all, but the idea of pushing one from your body, made you heave. 'It's worth it in the end,' your mommy friends tell you, but dealing with a hungry, crying, pooping small human who required constant attention was not something you were into. You didn't even get enough time to yourself!

 

Castiel seemed to ponder your words. When it hit him. “Your father is the leader of the Bonzo Business Men?” He asked. You turned, looking shocked.

 

“You didn't know?”

 

“Your last name sounded familiar, but there was never any news pictures of a daughter.” He thought a minute, before adding, “An attractive one at that.”

 

You blushed. Yes you had been compliments all evening, but they were either trying too hard, or not at all. This was sincere, and it made you feel butterflies. The alcohol was getting to you, for you replied, “Your quite an attractive one, too. Aren't you, Castiel?” You practically purred his name, and watched as his eyes lost some brightness at your praise.

 

You both continued your “playful” banter, before things escalated quickly, ending up in Castiel's Hotel room, awake through the entire night.

 

~~~FALSHBACK END~~~

 

“And let's just say, it didn't stay in Vegas.” Castiel smirked, still holding you on him as he finished the story, leaving out the delicious details.

 

“I'm sorry about your dad, Y/N.” Sam spoke up. Your father died almost a year ago, and you were coping. It helped when you had this beautiful being there along with you.

 

“Thank you, Sam.” You smiled at him. “That also explains this house. This is one we used for small getaways out of the office. It was normally ever really me and my old teacher here.” You reminisced, thinking of all the trouble you had caused out of boredom.

 

“I'm sorry.” Dean cleared his throat. “ _One?_ ”

 

“Yep, we had this one, the beach house in California, the vacay palace in Cabo, and the main homestead back in New York. We downgraded Cabo, but we passed along the N.Y. Residence to the rest of the B.B Men. The beach house went to Crowley, my father's right hand man, who now runs the company.” You spoke. Crowley was like an uncle to you. Yes, he was mean enough to whip the guys into shape, but around you, he was a big softie.

 

Sam seemed completely interested in your monologue, learning about your history, and where you came from. Dean was interested as well, but a little bored. Castiel was completely bored, hearing the talks over and over. Then he had an idea.

 

“What do you say we all go to the club? Celebrate your arrival?” Cas smiled, and when you looked at him, you could tell which one he was thinking about. You rolled your eyes playfully.

 

“Sure, I'm down.” Dean said, looking to Sam for an agreement. He didn't feel like it, he wanted to explore this house. Find as many secrets about your life that he could, or that you would let him.

 

The three of you looked at him, all pleading for his answer. He sighed.

 

“Fine.” A small cheer from everyone, and he smiled, rolling his eyes.

 

Castiel scooted you off of his lap, beckoning you to stand up. The boys followed your actions, standing up as well. The four of you walked to the bottom of the staircase, when Cas pulled you back against him.

 

“Honey bee, show our guests to there rooms, then when your done, come find me. Then we can discuss your...accessories.” Cas chuckled. Giving you a fast, hard smooch against the lips. You nodded excitedly. Turning towards the Winchester's you beckoned them to walk with you upstairs. Sam followed close behind, excited to see more of the home. Dean stood back, tapping Cas with a tense hand. Cas hummed, acknowledging Dean, while staring at your ass walking up the stairs.

 

“So, uh...what's the thing, between...you two?” Dean asked, not wanting to dive too deep to fast. But after the answer he got, he knew he needed to learn more.

 

“An agreement...of sorts.” Cas smiled, patting Dean back to go catch up with you and Sam. As he walked upstairs, he couldn't help the foreshadowing feeling in his stomach, and he wasn't sure if he was supposed to be surprised, or scared.

 


	2. What is this About?

**Summary for the Chapter:**

> Dean get's more information from you, but not enough to counter his curiosity. At the club, Dean finally gets all the information, and has to make a decision on what this will mean, and if he is interested.

Escorting the boys to their rooms wasn't that hard. Simply giving Sam the second door on the right of the hallway once you were up the stairs. Dean getting the third, as the first was a closet. The rooms were a good size, each with a king-sized bed, a desk and walk in closet. Sam's was a jungle green while Dean took the cool blue. You showed them that the bathroom was just down the hall on the same side, equipped with a big shower that gave off the _best_ water pressure, A Jacuzzi-like bath tub, a toilet that gave them the idea of why it was nicknamed a 'throne', and a double sinked counter, towels and extra toilet paper already laid out.

 

Sam gave you a hug, saying his thanks for the invite before going into his room to get situated. Dean had already gone in his. Just as you were to head to your shared bedroom with Cas, Dean came out of his room, looking to you.

 

“Y/N?” He asked, curiosity still on his mind. He couldn't shake that there was some hidden meaning behind Cas's message AND his earlier answer. He was hoping you would give him some more information.

 

“Yes, Dean? Is everything alright?” You asked, clasping your hands at your stomach and tilting your head, much like Cas would.

 

“Yeah, yeah. Everything is...amazing.” You beamed at his words, and he gave a small smile. “I was just wondering, what is between you and hot-shot?”

 

“Oh. Well, it is a relationship, of sorts...” You trailed off, smile fading as you looked for your words. Dean got a little frustrated.

 

“He said you weren't his wife OR his girlfriend. What kind of relationship is that?” He huffed. You smiled at his annoyance.

 

“Well, it does include love, and trust, much like a relationship would. Its more...open. In a way...” Dean was still baffled.

 

“'In a way?'” He repeated. You nodded at him. He opened his mouth to speak again, but you beat him to it.

 

“I can tell you're curious. This isn't something you're used to, I get it. I think it would be best for you to wait and see.” At this point you walked up to him, lightly trailing your hand lightly down his shoulder, grasping his forearm. He raised both eyebrows, looking tense. He wasn't sure if you were being friendly, or flirty, but when he saw the twinkle in your eyes, he found it was the latter. “Go get ready for tonight. It's just casual, but Cas always likes to make a show of himself. Speaking of which, I need to go. I'll see you later, k?” You winked, before moving away, taking your arm off of him, and he felt the lack of warmth that came with it. Nodding, he opened his door, taking one last peek of you, before heading in and closing it. You smiled, and walked across the way to your master bedroom.

 

The room was almost three times the size of the other rooms, that side of the hall splitting off to a smaller one. Down that hall was a glass door that led to an outside balcony. The door before it led to Cas's and your 'playroom'.

 

Walking into the bedroom, you heard noise from the open closet door, where Cas was located. He walked out though smiling when he heard the main door close, wearing only red dress pants, a little tighter than normal.

 

“Get the boys situated?” He asked. You nodded, going up to embrace him. He put his hands around your waist, kissing your neck, before moving up to your lips. You wrapped your hands around his neck, pulling him closer when he deepened the kiss. You gave a small moan when he bit your lip, attempting to follow him when he pulled away, straightening up. He smirked, and you swallowed.

 

“Dean is still a bit apprehensive about the stay. Sam seems okay, but it's hard to tell.” You spoke. Cas nodded, seeming indifferent about this information.

 

“I thought Sam might be the unsure one, but those boys will surprise you.” He walked to the bed, straightening the outfit he laid out for you. It was a simple gray top, medium length sleeves with the shoulders cut out. There was also your black skinny jeans, sewn in spots that would shine against the light.

 

“Should we go through with it?” You asked, doubt filling your mind. “They have no idea. What if they don't want to...” You trailed off. Cas frowned, but looked towards you, bringing you into a hug by your shoulders.

 

“If you don't want to, we don't have to. It can be just a normal stay, and nothing has to happen...at least, not with them.” He smiled into your neck, kissing it before giving a gentle bite. You sighed, shaking your head.

 

“It's not that _I_ don't want to, I'm just worried about them. Maybe we read their situations all wrong?” Cas frowned once more, moving to look into your eyes, contemplating his next move.

 

“How about I warn them, tell them a bit of why they're here, then ask their opinions. I can tell you don't want to go in head first without getting your feet wet... I'll pull them aside at the club. If they agree, great. If not, we'll pull out that part of the stay.” He looked for your answer.

 

“Sounds better. I don't want them to feel like we tricked them into this.” Cas nodded at your statement, A silent agreement. You decided to lighten the mood, pulling out of his embrace and walking towards your 'special' accessory display. You looked over them thoughtfully, Cas walking behind you and grabbing your hips, glancing over your shoulder.

 

“Which one would you prefer?” He asked, voice lower than before. You hummed, wondering yourself which would be better.

 

“I haven't seen Charlie in a while...” You spoke. You could feel Castiel's smirk, and he kissed your cheek from his position.

 

“Sounds wonderful. I thought a little reunion between you two was in order.” He spoke. You giggled at the hidden meaning, excited for a little reunion as well.

 

“Let's get ready then, can't have the boys waiting long.” You said, and Cas frowned at their mention, just wanting to take you into the 'playroom' already.

 

“Alright.” He sighed, and you both went to your separate areas, preparing for the night, your accessory planted in you handbag, ready for later.

 

~~~~~

 

Dean and Sam waited by the door, glancing out at the darkening sky. Sam had a small smile one his face, Dean still seemed tense.

 

“Come on, Dean!” Sam spoke, not looking away from the window.

 

“What?” Dean asked, though he knew where it was going.

 

“You were so excited to come and see Cas, and now you look like you're contemplating leaving.” Dean sighed, knowing that his brother was right. “Is something wrong?” Sam looked towards him.  


“It's not that anything is wrong, it's just...Don't you think this 'stay' is weird, or at least they're not telling us everything?”

 

“Of course.” Sam said, earning an eyebrow raise from Dean. He continued, “But I think it's weird for them too. This place, though well furnished, doesn't seem like it's been well occupied. Like there hasn't been many visitors for them. Maybe they are also nervous about our stay.” Dean swallowed, having not thought of it like that.

“You said it yourself, Dean. 'Live'.” Sam grinned, using Dean's earlier word.

 

“Okay, maybe you're right...” Dean said, but smiled afterwards.” But you're still a bitch.” He smirked, earning a smile from Sam.

 

“Jerk.” Sam said, smiling back at him. Dean was about to say more, but Cas came down the stairs, you right behind him.

 

“Ready to head out?” Cas asked, swinging his keys on his finger. His white dress shirt was unbuttoned at the top, showing off a bit of skin. When the boys saw you, they couldn't help but gawk. While your attire was not too revealing, it did hug your body in all the right ways, all while showing a generous amount of bust. Cas continued walking, toward the dining room, where the entrance to the garage was located. The three of you followed him, all while the boys attempted to nonchalantly peek at your ass. You could feel their gaze on you, so you swung your hips more than usual.

 

“I thought we could take the SUV.” Cas said as he opened the door and turned on the lights. Now illuminated, the boys could see everything. The back corner looked to be a workshop of some kind, a few mismatched tools laying over the table. The middle held a car covered in a sheet, so they couldn't see what it was, and a Harley Davidson. Finally, closest to them, was a red mustang, and a big white SUV, both looking brand-spanking-new.

 

Dean whistled. “Who's hog?”

 

“That would be mine.” You smiled. Looking at his gawking face. You looked too delicate to ride a motorcycle, but once Dean pictured it, he couldn't help but love to see you in action.

 

Cas got in the car, clearly not paying attention. “Hop in!” He called. Sam moved to sit on the side behind passenger, which would be where you sat, while Dean went behind driver.

 

As Cas started the engine, you fumbled with the radio controls. “In this household, passenger picks the music.” He explained, looking specifically at Dean, a playful smile on his face. The boys smiled back, just as you found your station.

 

“Hell yeah!” You announced, the first beats of Ed Sheeran's 'Shape of You' blasting through the car. Dean cringed a little, not what he was used to, and Sam smirked, watching his brother's distaste.

 

“'The club isn't the best place to find a lover, so the bar is where I go,'” You sang softly, grabbing Cas's right hand to hold in yours, as he pulled onto the street outside the driveway, the house disappearing behind you.

 

“'Me and my friends at the table, doing shots. Drinking fast and then we talk slow.'” He sang, even quieter than you. You peered at the boys in the backseat, having some hushed discussion, smiling at them. You hoped this night would go well.

 

~~~~~

 

Once pulled up to the club, Dean couldn't help himself at the name.

 

“' _Collared'?”_ He read. “This isn't some BDSM club, is it Cas?” He asked, adding a little laugh, though Sam visibly paled at the suggestion.

 

“Of course not,” Cas answered, smiling on his own. “This place is far too vanilla for that.” He added, noticing the strange looks from the boys. He looked over to you expectantly. “Sweetheart?” You grinned.

 

Rummaging through your small purse, only really holding your ID, phone, credit cards, a few bills, and your 'accessory'. Pulling it out, you gently place it around your throat, clicking back of the leather collar together. It held a small tag on it, a simple oval one, a few words engraved on it. Sam looked even more pale, and Dean more curious.

 

“Perfect.” Cas announced, loving the collar on you, and all that it entailed. “Everybody ready?” He asked, though waiting for no one as he jumped out of the car. You smiled sheepishly at the boys.

 

“Come on, guys. It's not that bad. I think you'll quite like it.” You said, before getting out of the car yourself. The boys shared a look, before shrugging and getting out. The walk to the door was quick, the well illuminated parking area only preparing your eyes for the purple lights shining above the entrance. There stood Kevin, the doorman. He didn't look like much, but he made sure everyone showed their ID's, at least, those he didn't know.

 

“Hey Cas, Y/N.” He smiled, before noticing Dean and Sam. “They with you?” Cas nodded eagerly, wanting in. Kevin smiled once more, opening the door. “Have fun boys.” he called towards Dean and Sam, closing the door once you were all inside.

 

“Woah...” Dean breathed, looking all over. To the right was a full bar, four bartenders working. There was a wall of booths about three-quarters to the back wall, which obviously went to the bathrooms. The dance floor took up the majority of open space, while a stage sat on the far wall parallel to the bar, where a DJ booth sat. Bodies and bodies dancing and grinding on each other on the floor. Dean was even more shocked to see a majority of the other patrons, including the bartenders, had collars with tags.

 

Sam looked pale once more, but his eyes sparkled from excitement under the purple and white lights overhead.

 

“Gabe!” Cas exclaimed, looking towards the man who was walking towards the group. As he stopped right in front of them, he gave Cas a bear hug, playfully rough. Cas laughed and returned the action.

 

“Y/N.” Gabriel said when he pulled away, giving you a smaller hug, which you gave back. He pulled back halfway, pulling your tag so he could read it. _Girls' Night,_ it read. He smirked. “She's been waiting!” He spoke, causing you to laugh. Gabriel pulled back fully when he noticed the boys behind you, still looking out of their element.

 

“Gabriel. I'm the owner.” He said, holding his hand out towards Dean, waiting for a handshake. Dean delivered, giving a firm shake with a quiet 'pleasure'. When it was Sam's turn, Gabe gave him a quick wink. Sam, though baffled, did not turn it down, instead giving a small smile, clearing his throat.

 

“Y/N, why don't you go see if your 'friend' is here. I'll be at the bar chatting with the guys.” Cas said, looking at you. You nodded, giving Cas a kiss on the corner of his mouth before walking away. “Boys.” Cas motioned towards the bar, an invite for a drink, which was not turned down by any means.

 

~~~~~

 

“Y/N!?” Charlie exclaimed, looking at you with bewilderment and excitement. You walked up to her, smiling and giving her a hug. She hugged back tightly, letting herself get comfortable with your body again. You pulled away, giving her a kiss on the cheek, making her frown.  


“If your tag says what I hope it says, then you know that won't be enough.” She scolded. You smirked as she looked at the tag, watching a smirk grow on her own lips. “Well then, what are we still down here for?” She asks. You motioned back to the bar.

 

“Having some guests over this weekend.” You said, giving a quick glance behind to make sure they weren't looking this way. They weren't so you turned back. “Friends of Cas.”

 

“I see...” She said, hand on her chin. “But I still don't see why that stops us...” She smiled. You smiled back, grabbing her hand in yours.

 

“You know what?” You said, having to speak up as the DJ upped the volume. “Me neither.” With that out of your mouth, Charlie gave you a quick peck, before using your hand to guide you behind the wall behind the bar, and up the stairs that led to a loft for employees, one she misused everyday.

 

~~~~~

 

The guys were making themselves comfortable, talking about memories from when Dean, Sam, and Castiel were all together, talking over a few empty shot glasses and beers. Sam's brows furrowed when he saw you being led away by a redhead, giggling as you two walked behind the wall behind the bar. He was going to mention it to Cas, but stopped when the group started laughing. He quickly hopped on the boat, not wanting to seem like he wasn't paying attention.

 

“Okay, okay. Have you guys ever had a blowjob?” Dean immediately busted out laughing.

 

“Dude, you are asking a stupid question right there.” He laughed out. Sam blushed, his own answer. Cas was the only one who knew what he meant, and played along.

 

“Yep, Gabe right here makes a mean blowjob.” He said, looking towards the boys. Dean stopped laughing, looking bewildered, but caught on as Gabriel pulled out a shot glass. Sam blushed even further.

 

“Don't you mean gives...” Sam trailed off. Cas started laughing, loving the confused glance of the brother. Gabe gave Sam an appreciative glance, slightly on the flirty side.

 

“I like this one.” He said to Cas, only making him laugh harder. Sam shrunk down, though hard to do with his height. Dean snickered, patting Sammy on the back.

 

“It's a shot, Sammy.” Dean clued Sam in. Not helping Sam anymore with his heated cheeks.

 

Gabriel started preparing enough for four, pulling out the necessary booze and layering them on top of each other, squirting a dollop of whip cream on each. Sam went to reach for one, but got stopped by Gabriel.

 

“This is a 'no-hands' drink.” He spoke, putting a shot glass in front of each of them. Sam's confusion deepened until he realized what a blowjob meant. Dean and Castiel already had their hands behind their backs, prepared to drink. Gabriel raised an eyebrow, daring Sam to do the same. With a sigh, he complied, and Gabriel followed suit. “One, two...three!” He exclaimed, diving in. Sam watched for a moment as the three of them wrapped their mouths around the rim of the glass, tilting their heads back to chug. Sam carried on, following the example. As the sweet booze flowed into his mouth, whipped cream mixing with it all, he swallowed. Once down his throat, he leaned down once more, dropping the shot glass on the table.

 

“My boy's first BJ, I'm so proud!” Dean announced, placing a hand on his heart and wiping away a fake tear with the other hand. This gained laughter from the other two, while Sam gave a bitch-face towards his brother, cheeks still tinted pink.

 

“Okay, okay!” Cas exclaimed once he gained back his breath. He looked back towards the booths, motioning to one that was empty. “Why don't we go have a seat?” He asked. Gabriel picked up on the message, excusing himself to go help other patrons. The boys walked to the table, the brothers squeezing in on one side while Castiel occupied the other.

 

“Thanks for the invite, Cas. It's really nice to take a break from the office once and a while.” Sam said, breaking the silence. Cas nodded.

 

“My pleasure. I'm just sorry about not getting in touch sooner.” Cas took a pull from his beer, thinking of how he was going to bring his intentions up.

 

“Y/N seems nice...” Dean trailed, not sure how to compliment his friend's partner/not partner. Castiel saw a window.

 

“Yes, she is. She helped prepare everything for your stay. It was partially her idea.” He said, as the boys raised their eyebrows. “She means well...and she couldn't help herself when I told her we hadn't been in touch.”

 

“We'll have to thank her when she gets back...” Sam said, brows furrowing as he remembered where you went...and with whom.

 

“Where is she anyway?” Dean asked, taking his own drink, and nearly spit it out at Castiel's answer.

 

“She's probably eating out her Mistress.” He said nonchalantly. Dean took a rough swallow, and Sam eye's looked as though they wanted to pop out of his skull.

 

“I'm sorry, her _what?_ ” Sam asked, not completely sure.

 

“Her Mistress.” Cas answered.

 

“And that's okay with you?” Dean asked.

 

“If it wasn't she would be right here.” Cas said, and sighed. “I'm sure you've realized our relationship is not one that is...common.” The boys nodded, waiting for Castiel to continue. “It is one that works for us, revolving mostly around..sexual activities. Sometimes, on the occasion, she craves something...different. Hence, Charlie.”

 

“Is she a redhead?” Sam asked for clarification

 

“Yes.”

 

“I saw her walking with her, being led to a room behind the bar.”

 

“Where they have their misadventures.” Castiel smiles. Dean still looked shocked. Turned on by the idea of you being with a woman, but shocked.

 

“So...this stay. Is it 'something different' as well?” Dean asked. Sam nearly chugged his drink, not wanting to be in the conversation but wanting to know the details.

 

“That was part of your stay, yes.” Cas answered. “But only if you two want to get involved.” Sam came up for air after finishing his bottle, eyes glazed from the affect of the alcohol. Dean still seemed skeptic.

 

“Is that why you mentioned our love lives? In your message?” Cas nodded.

 

“There will be no pressure. If you boys so wish, we can forget about this, I can tell Y/N, and we can go along with a normal weekend among friends.” Cas really didn't want to scare them. He could now see why you were so reluctant.

 

“I could go for it.” Sam spoke up, earning a pleased look from Cas and surprised glance from Dean.

 

“Dude! Wha...?”

 

“I'm 'living' Dean! Plus, blue balls makes this a hard thing to pass up.” Cas snorted, and Dean gave him a disgusted look.

 

“You're drunk.” He shook off the comment.

 

“You said it yourself. Drunk words are sober thoughts.” Sam nodded, not denying anything.

 

They fell into a short silence, Dean still sorting out his thought about this. His brother was in, but what should he make of it?

 

“Dean, what do you say?” Castiel asked, thinking Dean had enough time.

 

Dean sighed. “I guess I'm...”

 

**Notes for the Chapter:**

> Would anyone like a detailed smut for Charlie? I was thinking of making the next chapter one, but I also want to continue the story. Any requests?


	3. Getting to Know You

**Summary for the Chapter:**

> After a little 'playtime' With Charlie, Castiel decides it's time to go home. There you discover a little more about the boys than you were expecting to...at least for that night.

**Notes for the Chapter:**

> I'm sorry this took me so long to get up. I had technology problems, and i went away for a while, but its here now! Its is shorter than the others, but I hope to have the first sex scene up soon!

After another 15 minutes, the conversation between the boys returning to banter and story telling, you came back down from the loft. Your clothes were off kilter, and you hair clearly screamed 'SEX'. Your eyes also unfocused from your escapades with the redhead.

 

“Hey guys.” You sang, immediately going to Castiel to sit next to him, grabbing his arm to cuddle it. You were slightly tired from the few hours of 'playtime', but your body still craved more. You closed your eyes, missing the heated glances from the Winchesters across from you. Castiel gave you a few moments to calm down, before he nudged you. You opened your eyes, though he was looking at the brothers, giving you occasional glances as he spoke.

 

“This has been fun, but I'm quite tired.” He announced, adding a fake yawn to his speech. “Dear?” He looked at you. “Would you mind driving home? We had a bit to drink, and it would not be nice for our _guests_ to have a heart attack during their stay.” He pulled the keys out of his pocket, feigning un-coordination as he presented the keys to you. You took them from him.

 

“No problem.” You said, catching the sparkle in his eye that said 'you're mine when we get home'. You turned towards the boys, them pretending to look ready to go, but they had a similar look in their eyes. 'I can't wait for my turn', each of them said, so you could only assume they both said yes. You gave a mental jump of glee at this information, but your face only showed a small smile.

 

“Let's head out.”

 

~~~Time Skip~~~

 

The ride back was quiet, music down low, so everyone was focused mostly on their thoughts, or in your case, the road. You did let your thoughts travel, though, as well as your eyes. Looking into the front mirror to take a glance at each of the boys.

 

Sam, as well as tall, was muscular. His strong arms could probably pin you to a wall so easily. His slightly shy demeanor definitely did well to mask his personality, but something told you he might be the complete opposite in bed.

 

You would find out eventually.

 

Then there was Dean. Dean with gorgeous eyes that with a strategic wink could turn any woman into a puddle. While he had on some slight pudge, he still looked good enough to eat. You possibly might...

 

You were shocked out of your thoughts when a hand from beside you landed on your hip suddenly as you turned onto the house street, causing you to swerve to the left slightly. Thankfully no one was on the road this late. It was almost eleven after all.

 

After you corrected your driving, slowing as you neared the driveway, you sent a glare to Castiel, his grip slightly possessive on you.

 

“Cas, didn't you say you _didn't_ want to give our guests a heart attack?” You looked back to the road, your stern voice only an act. Castiel knew. You heard a snicker from behind you, and you looked to the mirror to find out it was Dean, and Sam sporting a small smile as well.

 

“You're right.” Castiel's eyes were dark with lust, a hunger that he was used to sating whenever he wanted. He turned to look at the boys, his features showing off a smirk, with eyes that said, 'back off'. “I'm sorry, friends. I'm not used to having to _contain_ myself around her. I'm sure you will know the feeling.” You blushed deeply at his final words, pulling into the driveway and up into the garage. Dean only gave a smirk in response, looking at you with appreciative eyes. Sam looked stone-faced, but answered in a quick nod. You parked the car, Cas already rushing to get out and get to your side. The boys stayed in a little longer after you got out to talk, though you didn't pay much mind when Cas pulled you into his body, pants tight and mouth already giving you orders.

 

“Bring them to their rooms, I'll be waiting _upstairs._ ” He gave a deep, lingering kiss to your cheek, and then rushed to the door to the house, no doubt to get ready. With two playrooms, you two set up a system for which mood the two of you would play. _Upstairs_ was the word for the third floor, which involved more strict dom/sub play. And more toys. You practically shook with anticipation

 

You looked back as the car doors shut, showing Sam and Dean. You smiled at them, and started walking towards the door. The eyes on your ass were expected, but it still made you feel powerful. You swayed your hips, exaggerating the movement even more as you went up the stairs. As you approached the spot between the doors, you felt the wind change behind you. You turned around just as Sam's hands rested on the wall beside your shoulders, caging you in.

 

“Can I help you, Sa-” You were immediately cut off as his lips crashed down to yours roughly, dominating over you so easily. His face pushed against you, causing your head to _thunk_ against the wall. Your hands went to cradle his head. Whether you meant it to push him away or bring him closer, you were not sure. His lips were so demanding in how they kissed you, your own lips struggling to keep up with his pace. With his hands around your hips, you could tell he wanted to grind himself against you as well, but he restricted himself, though just barely.

 

With a gasping breath, Sam pulled away from you after what felt like a three minute-long kiss, leaving you shaking from the powerful session. His body demanded that he pull you into his room, and ravish you before Cas said otherwise, but he knew it would be much more rewarding if he waited. With a smirk, he pulled away, giving out a rough sounding, 'goodnight,' to you, a nod to his brother, before walking into his room, his steps awkward due to his erection.

 

“Ugh, so over-dramatic.” Dean chuckled, causing you to look back over to him. His eyes had their own hint of lust, but his was more balanced, controlled. You guessed his being 'the oldest' helped. He swaggered over to you, his own arousal known, but still in the works. He cupped your face in one hand, the other holding his jacket. “Goodnight.” He said lowly, his lips coming forward to caress yours in a more passionate, slow dance. You let yourself fall into his hypnotic movement. Slow, yet with the same amount of control as Sam. Pulling away, he let his eyes convey some vulnerability, nothing you thought you would have seen on the man.

 

“Goodnight.” Your voice sounded so small, so fragile, and yet so wrecked with lust. Dean gave another smirk, biting his lip which only made you want to kiss him again. He pulled his hand away, using it to open the door to his room. With one more goddamn wink, he entered, retiring for the night.

 

You let yourself stay there for a minute, letting yourself recover. You closed your eyes and let yourself think about the differences in the two. Sam, who was so demanding, so different from his earlier shy demeanor. And Dean, the bad-boy looking type who was so soft. Yet, no matter which side of the spectrum they were on, they both couldn't compare to Castiel...

 

 _Castiel_... Your eyes busted open, remembering where Cas was, and what he was expecting.

 

“Fuck,” A breathy whisper from your lips, only reminding yourself what this weekend was about, and what was to come.

 

If you didn't know any better, you would've thought you were in heaven.

 


	4. The First of Many

**Summary for the Chapter:**

> You and Castiel finally have some playtime.

Walking up towards the door that Castiel would be waiting behind, you gained some anxiety. Yes, you two had done this song and dance for years now, but it still scared you not knowing what would happen. You always knew it would be mind-blowing, but for this specific door, it slightly scared you what he would be planning. The only hint you had was the belts and collar that were left on the bed, along with a note.

 

_Change the collar, and wear these. Do your counting. All will be fine, don't worry. R/Y/G._

_~Sir_

 

The signature at the end hinting that that was how you would call him. The R/Y/G the safety system. As for what you were wearing, you had a onyx strapless bra and panty lingerie set, the panties having a similar feature as the bra. Plus collars like the one around your neck, except they were also around your waist, ankles, and wrists. All with the same ring around them, which would allow him to chain you to any of the surfaces with a tether on them.

 

The other scary part was that there was no hint as to a specific scenario or scene. With a deep breath, after already having done your counting, you knocked on the door three times.

 

The door opened immediately after, showing you a Castiel, clad in only his pants from earlier. You bowed your head, showing him your submissive side.

 

No matter how nervous these sessions made you, they excited you twice as much.

 

“Hello.” Cas spoke, dominance as clear as day in his tone.

 

“Hello, Sir.” You greeted him back, softly. Your mind already heading into sub-space with the first word out of his mouth.

 

He smirked, well aware of this information. He moved to the side, welcoming you into the room. It was dark, aside from a few lights that lit up the specific places he could put you. There was also a small closet to the side, where all your toys, lubes, and ropes were hidden.

 

Once taking a few steps from the door, it was closed from behind you. Hands coming to wrap around your waist, gently pulling you to a hard, slightly hairy chest. The hands took turns, one going up while the other hand went down. As one hand was playing with your chest, squeezing and pinching each individual breast. The other was teasing, not going for the prize, as it stayed right above your slit.

 

“Where to first?” Castiel asked, voice deep, well controlled in his dominance.

 

Your heart thumped in your chest. He was giving you free reign, or at least, it _seemed_ like it.

 

“Wherever you wish, sir.” You kept your voice monotone, despite the way your body practically begs as you push yourself towards the hands that gripped you. His hands dipped into your slit, beginning to spread your wetness, making you release more. You knew you did the right thing.

 

“Such a good girl.” He purrs. Gently pushing you towards the 'X' bars in the room. Once there, he turned you around and moved your body into 'X' formation, while Castiel took the time to tether your wrists above your head, he moved slowly down, trailing his hands all over your body, even dragging his lips down a few times, before making his way to your ankles. Giving them more slack then he did your arms, he took time to look at his work. You didn't dare turn you head, even though you above all else wanted to look at him. Watch the way that his eyes would trail over your body, no matter how many times he has seen it.

 

“Color?” He checked in, walking into your peripheral view to the closet, set on getting the 'nine tails' whip, and getting that ass red.

 

“Green.” You spoke, giving him the permission he needed. After finding what he wanted from the closet, he walked over to you. First, trailing the tails along your body. Instinctively, you arched your back, letting the whip move along you better. Cas set it down after a moment, popping the clasps that you sewed into your underwear, making them easier to take off in these situations. He tossed them by the door knowing you would have to put them on before you two left.

 

“Count for me, darling.” He requested as he pick the whip up once more. You barely had time to say 'Yes, sir.' Before he struck you the first time.

 

“One!” You cried out, the sting only making you desire him more.

 

Castiel went to 20 before he felt your ass was red enough. He tossed the whip away, ready to retrieve you from your position. You were panting as he began to undo your legs, desire seeming to be your entire being.

 

“You were so good for me darling.” He spoke as he freed your hands. You tried your damned hardest to resist touching him, but as he turned you around so you faced him, you couldn't help but fall against him. He let you, thinking about how you would be so tired after the weekend, he might as well go easy on you.

 

“Color?” Cas asked, picking you up and sitting on a chair in the off-center of the room. He let you lay against him, deciding to let you find your own will.

 

“Green.” Your voice sounded so small, but your will was coming back to you. After another minute or two, you stood in front of Cas, but soon squated, giving him a perfect view of your wet pussy. “Can I suck your cock, Sir?” You asked, hands resting on his knees.

 

It was times like these Cas would never forget. How a lovely independent woman like yourself ever fell into his hands, he would never know, but he still thanked whoever was up there for it.

 

Cas gave a deep groan, his hand coming to rest in your hair. “Of course, sweetheart. Suck my cock.” He let your hands undo the top of his pants, his painfully hard member being the only thing in your sights as you moved your head forward, giving the head a few kitten licks before going as deep as you could. Castiel groaned, the feeling of your mouth over him never ceasing to bring him such pleasure. He bent over you, unsnapping the clasps of your bra before throwing that by the door with your panties. His breathing grew deeper as you sucked him off, head sliding up and down on him. It was too soon that he couldn't take anymore, and he tapped your head, your signal to stop. You let his cock fall from your mouth, looking up at him expectantly. He patted his lap, and you climbed on him, laying your back to his front.

 

He spread your legs over his own, making yours spread wider. His dick was trapped between his front and your butt, so you wiggled yourself against him, but a quick slap to your inner thigh halted your movement.

 

“Here are your orders.” He started. “First, you are going to come with your legs spread, like this.” As he spoke, his hand made a slow trail towards your pussy, making you jump when it made contact. “Then you are going to come again, with my mouth on that sweet little cunt.” You gave a moan at his words, looking forward to him following through. “And finally, you're going to come split on my cock. Think you can handle that?” He asked as two of his fingers pushed into you, making you whine at the intrusion.

 

“Y-yes Sir.” He gave a low growl at that. Your voice so small and needy, yet so prepared to please.

 

“Good girl.” You would have beamed at his praise, were you not rocking your hips to his hand. His other arm was wraped around your front, keeping you against him as he kissed into the back of your neck, whispering how pretty you were, how wet you were, how sweet you would feel on his cock. You were so close, but only when he wrapped his hand loosely around you throat did you come. Spasming around his fingers before he removed them, taking them to his lips to get a taste.

 

“Get up.” He growled around his fingers in his mouth, waiting for you as you stood, getting up right after you only to push you back do onto the chair. He kneeled in front of you, gently moving your legs to hang over his shoulders as he gave you time to come down. Once you did, you gave him the go ahead, and he dove right in.

 

His mouth was everywhere it felt like. Tongue inside of you, lips sucking your clit. It wasn't long until you were on the brink again. He used his thumb to circle your clit as he tongue-fucked you through orgasm, collecting your all your sweet essence.

 

He didn't give you time to recover, having waited long enough himself. He stood, shucking off his pants as you stood on shaky legs, letting him man-handle you to the nearest wall. You jumped into his arms as he pushed you against the wall, lips slamming to meet yours in a searing kiss. His hand trailed down, taking himself to your entrance, before letting you slide down his length. You both moaned at the intrusion, so used to eachother, but you both know you could never get over this moment in your relationship.

 

Cas took turns fucking you and making love to you. Your tight heat making it hard to conentrate on how he wanted this to go. You didn't mind though. You were willing to let him take what he needed. And that was you.

 

You were close too, so when his hand wrapped around your throat once more, you knew you would be done for soon.

 

“Sir.” He looked at you then, eyes softening as he looked into your eyes. “Come for me,” You begged, and his eyes took a dark turn. “Please come.” It was then he knew he had to fuck you, get you as close to the edge as he was. His hips would snap up, meeting yours as you both got close.

 

With a final squeeze to your throat, you came, nearly screaming if it wasn't for his hand. Your orgasm triggered his own, and he came inside of you with a roar. Both of you never feared this, as you had the implant. This was the one thing you couldn't get rid of, loving the intimacy it brought you.

 

When you came down, you felt bone tired. These sessions normally left you that way. Castiel, being the ever caring gentleman that he was, made sure to clean you up and put a robe on you and him before you left the room. You were nearly asleep in his arms as he carried you down the steps, and into the hall. Being as gentle as he could, he put you to bed, tucking you in. It was nearly two in the morning when he checked the clock. He sat in the chair across the room, watching you, and figuring out how he would enact the plan with the boys.

 

**Notes for the Chapter:**

> I have not given up on this. It shall be completed


	5. Dean's Turn 1/3

**Summary for the Chapter:**

> Dean gets his first real taste of what you can do.

**Notes for the Chapter:**

> I AM SO SO SO SORRY THIS HAS BEEN SO LATE!!! I knew I was going to finish it, it was just a matter of when. There will be a second part to this chapter...possibly a third? not sure yet. But I am just thankful for you who are reading! It really gives me a warm and fuzzy inside knowing people read my work.

Dean's Turn

As you woke up, you saw the note written in big font on the side table. You grew even more curious when you saw, not Castiel next to you, but instead a schoolgirl outfit. The same one you wore when cosplaying and 'playing' with Cas. You were definitely curious.

Getting dressed in the outfit and walking in the hall, you saw a note taped on Sam's door. Getting closer, you saw it was addressed to you.

~Y/N  
Castiel and I have gone out of town to grant you and Dean the upmost of privacy. I feel that it may be hard to explain for him, so here is your hint.

Dean has a Daddy kink.

I can't wait for my turn ;)

~Sam

A Daddy kink? You had experimented with Castiel once, but with him, it wasn't your cup of tea. Maybe it will be different with Dean? You thought.

You walked down the stairs slowly, wanting to give Dean enough time to prepare himself. You stopped though when you heard him talking on the phone.

“...sure this is ok?” The question helped you know that he was second guessing it again. You walked further into the kitchen, but were quiet enough so that he couldn't hear you, with his back to you, still on the phone.

“She hasn't come down yet. Is that a bad sign?” You rolled your eyes with a smile at his concern. You decided that it was time to show that you were ready yourself. You walked the rest of way to him, which was only a couple of yards, and hugged his back. He flinched at your contact, a small noise leaving his lips. You snuggled into his back as he relaxed, finally muttering a “I'll talk to you later.” before hanging up the phone.

“Hi.” You whispered as he slowly turned in your arms. He still looked nervous, perhaps even more so than when he was on the phone. You looked towards the kitchen, seeing that he had made breakfast. Pancakes with hash browns and bacon. You were surprised, used to doing that yourself. 

“Shall we?” He said as he turned out of your embrace to get plates set up.

~

At the table, he still seemed so high strung, you were contemplating getting him a beer. You were so curious about his ideas of what he wanted today to go like, though, so you didn't want to get alcohol involved. You decided to start off lightly.

“So, I saw a note on Sam's door earlier.” You started, hoping maybe he saw it to. From the blush on his face, he didn't.

“What did it say?” He questioned, still digging into his breakfast.

“It just gave me a heads up.” You said, not wanting to give it away. He looked at you through his lashes, mouth still chewing, wondering what you were up to. Your face gave nothing away, however, only irking him further.

It took a few minutes of silence for breakfast to be eaten, which you delighted in, but made Dean anxious. When is she going to make a move? 

Dean was getting ready to stand up and take the dishes away, but you beat him to it, launching yourself up from the chair. 

“Don't worry, Daddy. I got it.” You said as you gathered the dishes. You made a show of bringing them to the kitchen, bending down over the table to grab them from his side, and bending over the sink to put them in. He looked paralyzed, still shocked of the words that came out of your mouth.

As you washed the dishes, Dean walked up behind you, his hands landing on your hips, simply holding them. You continued to wash, though with his breath fanning your neck, it was becoming hard to concentrate.

“What did you call me?” His voice was low, but still curious, as though he wasn't sure himself. You finished the dishes few seconds later, and turned around in his grasp. His eyes looked hopeful, excited that this could really be happening.

“I called you Daddy.” You said simply, gazing into his eyes. “You like being called that, don't you?” It was your turn to be unsure, but the way he was looking at you was a clear indication he loved it.

“Oh, sweet-heart. You have no idea..” His hand traveled up, cupping your face as he looked between your lips and your eyes. You gave him a nod, giving consent to do what he was craving to do.

You closed your eyes as you saw his head begin to bend down, and wrapped your arms around his neck when his lips met yours. His hand cupping your face went back to your hip, beginning to massage the flesh through your skirt. You side-stepped away from the sink, getting a little ways away before grabbing his hands and jumping so you could sit on the counter. His hips pressed flush against yours, and you could feel the outline of his hardening cock against your core.

“Mmm, Daddy...” You moaned as he ground himself against you, his own grunt falling from his lips as he pulled back. Looking into your eyes, he took note of the anticipation that was held in them. He could feel his own anticipation thrumming through his veins, going south in no time.

“Yes, babygirl?” He growled. 

“Where should we take this?” You asked. You knew Castiel wouldn't be ok with going to your shared room, but Dean's guest room should work.

Instead of answering, Dean started carrying you into the living room, dropping you onto the couch on your knees, Your head just above the crotch of his pants.

“We'll go to my room soon, babydoll.” He started, as though he had read your mind. His hands were busy unbuckling his belt. “I just need that pretty mouth on my cock, first.” you grabbed his knees, slowly making your way up as he finished undoing his pants.You looked up at him, into his eyes as he pulled himself out, giving a few tugs before letting it stand on its own.

It wasn't completely hard, but you had a way to fix that. As you trailed your hands up, you brought your head down, letting your lips touch the tip before taking him in. You gave a gentle lick to the slit, before trailing your tongue around to the bottom vein, keeping it in that position as you brought your mouth over him farther.

“Oh.. shit.” Dean exclaimed as you relaxed your throat enough to take him in. “Fuck..baby...” You pulled back as he dragged his hand across your jaw, pulling you off of his member.

“Yes, Daddy?” You asked, before giving a final lick from the base of his cock to the tip. You looked up at him, watching as he took a seat on the couch, pants down to his ankles, and cock standing proud. You took the time to crawl slowly towards his new placement, placing your hands on his legs and dragging yourself up. You stayed in your position, waiting for him to say anything. Finally, when he was about to, you didn't give him the chance as you quickly moved your mouth back onto him.

He released a moan at your surprising action, a hand going to your hair to guide you up and down as you continuously sucked him off. This went on for a few minutes, your lips tingling, all while he moaned out praises and incoherencies, before he pulled you off him once more. This time, he dragged you by the hair to your feet, your knees falling onto the couch, spread by his own. He dragged the your skirt up, prepared to take off your underwear, only to find there was nothing blocking his view of your bare pussy. 

He could see the glistening of your wetness in your folds, and even on your thighs from where it spread.

He groaned in satisfaction. “Good girl.” His hand that remained in your hair moved your head a final time, so that your lips met his in a bruising kiss. He let the hand that wass in your hair travel down, to where the other rest on your hip. Slowly, you sat down, his cock coming into direct contact with your soaking hole, offering little resistance, before slipping through. Both of you gave a mighty moan at the initial intrusion.

As the initial high fell, you could feel Dean dragging your hips up, and you helped him, raising up before slowly sinking yourself down, feeling the slight stretch and reveling in the feel.

“Daddy...” You moaned. Dean looked at your, his eyes searching yours to get his attention, before he let his lips travel to yours once more.

Slowly, you two created a rhythm, one full of moans, kisses, heat, sweat, and a whole lot of bouncing.

When you felt your peak getting closer, you pushed harder. Dean following your rough bounces by helping you along, rubbing your clit until you unleashed a powerful moan, a signal of your orgasm. In your pulsing walls, Dean found his own release, grunting into your throat as he rested his head there. Both of you staying still, blissfully unaware of the world in either's embrace.

Dean gave a gentle slap to your rear as a sign for you to get up. You gave a little wiggle of your bottom half first, which caused small moans to erupt from both of your throats. You gently got off of Dean, stretching your arms above your head as you waited for him to get up as well. Dean, once up, simply pulled his pants up, while you used some tissues from the coffee table to wipe yourself.

“Well that was fun.” Dean beamed, getting close to you and pulling you for a kiss. “But I say we get fully naked next time. Whaddya princess?”

You smiled, excited about a next time already. “Yes, Daddy.”


	6. Dean Part 2

**Summary for the Chapter:**

> Dean gets to spend more time with you, and gets a taste of what you have to offer.

You and Dean spent the rest of the morning calmly. When lunch came around, he took the time to make some burgers for the both of you. You also made another favorite of his, apple pie, which you shared, though the amounts may have been a bit unequal.

 

It was early in the afternoon when you two were lying on the couch, watching your favorite movie. Dean however, didn't seem too interested.

 

He had his arm wrapped around you, your legs tucked under you at an angle, holding popcorn that was mostly eaten out of Dean's boredom. Your eyes were glued to the screen, trying to find details you maybe hadn't before.

 

Dean had other ideas though.

 

Slowly, he made a reach for the popcorn, slowly prying it from your grasp. He placed in on the coffee table. Sitting halfway off the couch, he decided he might as well go for it, gently grapping your legs and moving them so you were sitting on your butt, legs hanging over the edge. You only spoke up when you felt his hand travel towards the bottom of your skirt.

 

“Daddy, Whatcha doin'?” You asked, your voice quiet, eyes still stuck to the movie. His hand stopped in it's tracks, as he looked at you, waiting for you to notice. It took a while, but you finally turned toward him as he squeezed your knee firmly.

 

Without saying anything, he separated your legs, kneeling before you, and moved your skirt up to your stomach. “If you wanna keep watching your film, go ahead.” He spoke. He got closer to your core, gently breathing on it before giving you orders. “Tell me how it ends, I'm just gonna have a snack.” He winked up at you, before using his free hand to tilt your chin up to the TV.

 

You sat a few moments in anticipation, Dean waiting until you had relaxed enough into the movie before licking a stripe from your core to your clit.

 

“Ah!” You moaned, as Dean licked stripe after stripe of your cunt. You reached your hand down to grab into his hair, also trying to look down, but one of Dean's hands stopped you.

 

“Focus.” _Lick._ “On.” _Lick._ “The.” _Lick_. “Movie.”

 

You tried. Boy, did you try. But every lick and suck straight to your core was driving you absolutely mad.

 

“Daddy~!” You shouted when you finally reached your peak. Dean kept eating you out through it, launching you into another orgasm not long after. You could tell he was going to go into a third, but the sensitivity was starting to get to you.

 

You started trying to push his head away, but all this got you was a nip to the inner thigh. Just when you thought you might come again, he moved away. You whined, but then his hand just took over the job. He kneeled between your legs, one hand working you closer, but never getting you over that peak. His other hand was put around the back of your neck gently, and he brought his head up to yours.

 

“You ever squirt, sweetheart?” He asked. You gave a small nod, moving your hips in time with his fingers as they thrusted into you. He gave a smirk. “Think you can do that for me? Think you can squirt all over my arm?” He whispered into your ear. You gave a moan at the thought. His hand started going faster, working harder to bring you to that peak... Just before he slowed down again. You gave a moan of betrayal, only earning a dark chuckle from him.

 

“C'mon, babygirl. Let me feel you.” You moaned at his words, feeling yourself getting closer with not only his actions, but words as well. “I want you to get this couch soaking.” His fingers had finally started to go faster it was only a matter of time before you exploded. “You gonna come?” He asks, as if he had to. You could only nod, words failing you as you felt the knot in your stomach tightening and tightening.

 

“Come.” He demanded into your ear with a rough voice, launching you into an explosive orgasm, Dean getting what he wanted from you. You gushed into his hand, wetness coating his arm up to a little above his elbow. You could only moan as you came down, trying to remove Dean's hand, from where it stayed, fingers still deep inside you.

 

“Such a good girl.” He cooed once you were down from the high. His fingers took their time from out of you, tickling your insides as you felt them being removed. You slumped into the couch, feeling the squelch as you sat in your own juices. Dean gently picked you up, carrying you up the stairs to his guest room, where he laid you down. He helped you out of your clothes before taking off his own down to his boxers, laying down next to you and manuvering you until he was spooning you from behind.

 

“But Daddy...” You protested when you felt his erection against your back.

 

“I'll be fine.” He said. You looked back at him confused. “You take a nap, it'll be there when you wake up.” he chuckled. He continued to speak lightly, lulling you into a light slumber.

 

**Notes for the Chapter:**

> PART THREE WILL BE ADDED. I suck at ending chapters I am sorry.


End file.
